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Boston to NYC city

Hi guys i have a customer that is flying into Boston in October has done Boston and Cape Cod but is wanting to drive to NYC he really wants to visit Stockbridge which i am struggling with making an itinerery i have 6 nights to fill for this drive can anyone suggest stops along the route customers like small towns and small old hotels any suggestions ?

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Stopped at Newport RI which features the famous mansion walks and had a lovely town centre,

Then Mystic (Mystic pizza film) gorgoeus qaint town and great Maritime musuem,

New haven., pay a visit to Yale University

Then finished off in Stamford which is good for shopping, not a huge amount to do here really but get there earliy enough and he can drop his car hire off here and take the Amtrak into NYC which is much easier!